5920
D. K. Barma et al. / Tetrahedron Letters 45 (2004) 5917–5920
(
b) Barma, D. K.; Baati, R.; Valleix, A.; Mioskowski, C.;
J ¼ 4:0 Hz, 1H), 4.12–4.05 (m, 1H), 3.80 (s, 3H), 2.92–2.82
(m, 1H), 2.76–2.68 (m, 1H), 2.48 (d, J ¼ 6:0 Hz, 1H), 2.10–
Falck, J. R. Org. Lett. 2001, 3, 4237–4238; (c) Falck, J. R.;
Barma, D. K.; Baati, R.; Mioskowski, C. Angew. Chem.,
Int. Ed. 2001, 40, 1281–1283; (d) Barma, D. K.; Kundu,
A.; Baati, R.; Mioskowski, C.; Falck, J. R. Org. Lett.
1
3
2.02 (m, 1H), 1.88–1.87 (m, 1H); C NMR (100 MHz,
CDCl
71.29, 62.06, 53.39, 35.48, 34.71, 31.80. Compound 29
3
) d 169.19, 141.20, 128.65, 128.61, 126.28, 126.23,
1
2
002, 4, 1387–1389; (e) Baati, R.; Barma, D. K.; Falck, J.
R.; Mioskowski, C. Tetrahedron Lett. 2002, 43, 2179–
181; (f) Barma, D. K.; Elayadi, A.; Falck, J. R.; Corey,
D. R. Bioorg. Med. Chem. Lett. 2003, 13, 1333–1336.
2. Stereoselective synthesis of (Z)-a-chloroacrylates: Barma,
3
(anti-isomer, 71%): H NMR (300 MHz, CDCl ) d 7.41–
7.25 (m, 5H), 6.76 (d, J ¼ 15:0 Hz, 1H), 6.28 (dd, J ¼ 15:0,
2
6.6 Hz, 1H), 4.80–4.70 (m, 1 H), 4.34 (d, J ¼ 6:6 Hz, 1H),
1
3
3.83 (s, 3H), 2.67 (d, J ¼ 5:4 Hz, 1H); C NMR (75 MHz,
1
CDCl
126.88, 125.94, 73.69, 59.49, 53.30. Compound 29 (syn-
3
) d 169.05, 136.07, 134.06, 134.06, 128.75, 128.35,
D. K.; Kundu, A.; Zhang, H.; Mioskowski, C.; Falck,
1
3
isomer, 29%): H NMR (300 MHz, CDCl ) d 7.41–7.25
1
1
(m, 5H), 6.74 (d, J ¼ 15:0 Hz, 1H), 6.20 (dd, J ¼ 15:0,
6.6 Hz, 1H), 4.80–4.70 (m, 1H), 4.43 (d, J ¼ 5:4 Hz, 1H),
1
3
4. Nunez, M. T.; Martin, V. S. J. Org. Chem. 1990, 55, 1928–
3.81 (s, 3H), 2.67 (d, J ¼ 5:4 Hz, 1H); C NMR (75 MHz,
3
1
932.
CDCl
126.88, 125.89, 73.40, 61.77, 53.36. Compound 30 (anti-
) d 169.61, 136.00, 133.94, 133.94, 128.75, 128.41,
1
1
5. Nagai, W.; Hirata, Y. J. Org. Chem. 1978, 43, 626–630.
6. A catalytic system utilizing Mn powder to recycle Cr(III)
to Cr(II) gave poor yields: F u€ rstner, A.; Shi, N. J. Am.
Chem. Soc. 1996, 118, 12349–12357.
1
3
isomer, 75%): H NMR (400 MHz, CDCl ) d 7.65–7.63
(m, 2H), 7.54–7.51(m, 2H), 5.12 (dd, J ¼ 7:6, 4.8 Hz, 1H),
4.36 (d, J ¼ 7:6 Hz, 1H), 3.81 (s, 3H), 3.13 (d, J ¼ 4:8 Hz,
1
3
1
1
1
2
2
7. Shen, Y.; Xin, Y.; Zhao, J. Tetrahedron Lett. 1988, 29,
3
1H); C NMR (75 MHz, CDCl ) d 169.36, 142.79, 127.62,
6
119–6120.
127.62, 125.61, 74.81, 58.92, 53.44. Compound 30 (syn-
1
8. Lewis, F. D.; Quillen, S. L.; Hale, P. D.; Oxman, J. D.
J. Am. Chem. Soc. 1988, 110, 1261.
9. Heck, R. F.; Nolley, J. P., Jr. J. Org. Chem. 1972, 37,
3
isomer, 25%): H NMR (400 MHz, CDCl ) d 7.65–7.63
(m, 2H), 7.54–7.51(m, 2H), 5.26 (dd, J ¼ 5:6, 4.4 Hz, 1H),
4.46 (d, J ¼ 5:6 Hz, 1H), 3.74 (s, 3H), 3.11 (d, J ¼ 4:4 Hz,
1
3
2320–2322.
3
1H); C NMR (75 MHz, CDCl ) d 168.64, 142.43, 127.15,
0. Bode, J. W.; Doyle, M. P.; Protopopova, M. N.; Zhou,
Q.-L. J. Org. Chem. 1996, 61, 9146–9155.
1. Banwell, M. G.; Cameron, J. M.; Corbett, M.; Dupuche,
J. R.; Hamel, E.; Lambert, J. N.; Lin, C. M.; Mackay, M.
F. Aust. J. Chem. 1992, 45, 1967–1982.
127.15, 125.92, 73.77, 62.41, 53.44. Compound 31 (syn-
1
isomer, 34%): H NMR (400 MHz, CDCl ) d 7.46–7.31
3
(m, 5H), 6.96 (s, 1H), 6.88–6.82 (m, 2H), 5.16 (s, 2H), 5.07
(d, J ¼ 6:4 Hz, 1H), 4.43 (d, J ¼ 6:4 Hz, 1H), 3.91 (s, 3H),
1
3
3
3.67 (s, 3H), 2.88 (br s, 1H); C NMR (100 MHz, CDCl )
2
2
2
2
2
2. Xu, C.; Liu, G.; Zhang, Z. Synth. Commun. 1987, 17,
d 168.60, 149.82, 148.53, 137.04, 131.24, 128.70, 128.70,
128.04, 127.41, 127.41, 119.18, 113.78, 110.26, 75.00,
1
839–1843.
3. Zebovitz, T. C.; Heck, R. F. J. Org. Chem. 1977, 42, 3907–
909.
4. Jia, C.; Lu, W.; Kitamura, T.; Fujiwara, Y. Org. Lett.
999, 1, 2097–2100.
71.06, 62.89, 56.17, 53.13. Compound 31 (anti-isomer,
1
3
66%): H NMR (400 MHz, CDCl
3
) d 7.46–7.31 (m, 5H),
6.96 (s, 1H), 6.88–6.82 (m, 2H), 5.17 (s, 2H), 5.00 (d,
1
J ¼ 8:0 Hz, 1H), 4.37 (d, J ¼ 8:0 Hz, 1H), 3.91 (s, 3H),
1
3
5. Villieras, J.; Disnar, J. R.; Masure, D.; Normant, J. F. J.
Organomet. Chem. 1973, 57, C95–C98.
3
3.67 (s, 3H), 2.88 (br s, 1H); C NMR (100 MHz, CDCl )
d 169.57, 149.79, 148.62, 137.08, 131.94, 128.70, 128.70,
128.04, 127.41, 127.41, 119.64, 113.64, 110.37, 75.32,
71.06, 59.26, 56.17, 53.26.
1
6. Compound 27 (anti-isomer, 75%): H NMR (400 MHz,
CDCl
3
) d 7.31–7.18 (m, 5H), 4.21 (d, J ¼ 6:8 Hz, 1H),
.04–3.98 (m, 1H), 3.80 (s, 3H), 2.92–2.82 (m, 1H), 2.76–
.68 (m, 1H), 2.48 (d, J ¼ 6:0 Hz, 1H), 2.10–2.02 (m, 1H),
4
2
1
1
3
27. Roux-Schmitt, M.-C.; Seyden-Penne, J.; Wolfe, S. Tetra-
hedron 1972, 28, 4965–4979.
28. Reformatsky review: F u€ rstner, A. Synthesis 1989, 571–
590.
29. Review of chromium-mediated Reformatsky reactions:
F u€ rstner, A. Chem. Rev. 1999, 99, 991–1045.
1
3
.88–1.87 (m, 1H); C NMR (100 MHz, CDCl
3
) d 169.36,
41.36, 128.65, 128.61, 126.28, 126.23, 71.18, 59.60, 53.26,
1
4.71, 34.71, 31.60. Compound 27 (syn-isomer, 25%): H
3
NMR (400 MHz, CDCl ) d 7.31–7.18 (m, 5H), 4.32 (d,